Tom Reilly (ZACH BRAFF) and Sofia Kowalski (AMANDA PEET) are a happily married couple who live in New York and are expecting their first baby. He's an up and coming chef, yet they're worried that her leaving a law firm to stay home and take care of their child might leave them financially strapped. Those worries are only worsened when Tom stands up to his mean and demeaning boss and thus is fired. With nowhere else to turn, they decide to move back to Ohio where they'll live near her parents, Bob (CHARLES GRODIN) and Amelia (MIA FARROW), and Tom will take a job working for Bob's advertising firm.
As Sofia takes care of their new child at home and befriends young latchkey neighbor Wesley (LUCIEN MAISEL), Tom tries to adjust not only to their suburban, white bread surroundings, but also the creative yet strange mentality at work, where employees like Manny (FRED ARMISEN) sort of seem far out there.
Seemingly more centered is Tom's immediate supervisor, Chip Sanders (JASON BATEMAN), a former cheerleading squad teammate of Sofia's who's now wheelchair bound. While Chip seems motivated to help his new subordinate succeed, Tom starts to feel otherwise, particularly when he learns that Chip once slept with Sofia long ago. Accordingly, and based on other things that occur, Tom starts to believe that Chip is trying to sabotage him at work and at home.
From that point on, he tries to prove that's exactly what's occurring, as well as that Chip is faking his handicap, all of which makes him look bad in the eyes of others, including Sofia.